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Record Information
Version3.6
Creation Date2006-08-12 23:44:01 UTC
Update Date2016-02-11 01:06:23 UTC
HMDB IDHMDB03559
Secondary Accession NumbersNone
Metabolite Identification
Common NameGibberellin A3
DescriptionGibberellic acid, also called Gibberellin A3, GA, or GA3, is a very potent hormone whose natural occurrence in plants controls their development. Since GA regulates growth, applications of very low concentrations can have a profound effect while too much will have the opposite effect. Gibberellic acid is a hormone found in plants. Gibberelic acid is a simple gibberellin promoting growth and elongation of cells. Affects decomposition of plants. Helps plants grow if used in small amounts, but eventually plants grow a tolerance for it. Gibberellic acid stimulates the cells of germinating seeds to produce mRNA molecules that code for hydrolytic enzymes.
Structure
Thumb
Synonyms
ValueSource
(+)-Gibberellic acidChEBI
GA3ChEBI
Gibberellic acidChEBI
Gibberellic acid ga3ChEBI
GibberellinChEBI
Gibberellin 3ChEBI
GibberellinsaeureChEBI
2b-Hydroxygibberellin 1HMDB
BerelexHMDB
BrellinHMDB
Gib-solHMDB
Gib-tabsHMDB
Gibb-tabsHMDB
GibberelateHMDB
Gibberelic acidHMDB
GibberelinHMDB
GibberellateHMDB
Gibberellin 1HMDB
Gibberellin XHMDB
GibberellinsHMDB
GibberillateHMDB
Gibberillic acidHMDB
Chemical FormulaC19H22O6
Average Molecular Weight346.3744
Monoisotopic Molecular Weight346.141638436
IUPAC Name(1R,2R,5S,8S,9S,10R,11R,12S)-5,12-dihydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-13-ene-9-carboxylic acid
Traditional Namegibberellic acid
CAS Registry Number77-06-5
SMILES
[H][C@@]12CC[C@]3(O)C[C@]1(CC3=C)[C@@H](C(O)=O)[C@]1([H])[C@]3(C)[C@@H](O)C=C[C@@]21OC3=O
InChI Identifier
InChI=1S/C19H22O6/c1-9-7-17-8-18(9,24)5-3-10(17)19-6-4-11(20)16(2,15(23)25-19)13(19)12(17)14(21)22/h4,6,10-13,20,24H,1,3,5,7-8H2,2H3,(H,21,22)/t10-,11+,12-,13-,16+,17+,18+,19-/m1/s1
InChI KeyInChIKey=IXORZMNAPKEEDV-SNTJWBGVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentC19-gibberellin 6-carboxylic acids
Alternative Parents
Substituents
  • 20-norgibberellane-6-carboxylic acid
  • Diterpene lactone
  • Gamma butyrolactone
  • Dicarboxylic acid or derivatives
  • Tertiary alcohol
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point234 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5 mg/mLNot Available
LogP0.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility1.95 mg/mLALOGPS
logP0.66ALOGPS
logP0.35ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-0.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity86.42 m3·mol-1ChemAxon
Polarizability48.43 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r7-1962110000-9177c556fa6efad1c774View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-06r6-1962210000-a42d3ddb71fce133830eView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-067l-0963100000-6f900069528062a9617dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013644
KNApSAcK IDC00000003
Chemspider ID7995349
KEGG Compound IDC01699
BioCyc IDCPD-6224
BiGG IDNot Available
Wikipedia LinkGA
NuGOwiki LinkHMDB03559
Metagene LinkHMDB03559
METLIN ID6954
PubChem Compound9819600
PDB IDNot Available
ChEBI ID682248
References
Synthesis ReferenceLischewski, Manfred; Adam, Guenter. Gibberellin compounds. Ger. (East) (1979), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Yamaki T, Takeda K: [A simple bioassay method of urinary indoleacetic acid, a cancer growth factor] J UOEH. 1986 Mar 20;8 Suppl:297-302. [3460143 ]